Copper-catalyzed cyanation of aryl iodides with α-cyanoacetates via C-CN bond activation.
نویسندگان
چکیده
A Cu(I)-catalyzed cyanation reaction of aryl iodides with α-cyanoacetates is reported herein, which uses α-cyanoacetates as the nontoxic and easy-handling CN source through copper-mediated C-CN bond cleavage. This reaction enables access to aryl nitriles with an array of functional groups on the aromatic ring in good to excellent yields.
منابع مشابه
Photoinduced, Copper-Catalyzed Carbon-Carbon Bond Formation with Alkyl Electrophiles: Cyanation of Unactivated Secondary Alkyl Chlorides at Room Temperature.
We have recently reported that, in the presence of light and a copper catalyst, nitrogen nucleophiles such as carbazoles and primary amides undergo C-N coupling with alkyl halides under mild conditions. In the present study, we establish that photoinduced, copper-catalyzed alkylation can also be applied to C-C bond formation, specifically, that the cyanation of unactivated secondary alkyl chlor...
متن کاملCopper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines
We report herein studies on copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines. Treatment of N-H ketimines having an α-sp(3) hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C-C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction ...
متن کاملPalladium-catalyzed direct cyanation of indoles with K(4)[Fe(CN)(6)].
Direct cyanation of indole derivatives has been achieved with nontoxic K(4)[Fe(CN)(6)] as cyanating agent through Pd-catalyzed C-H bond activation.
متن کاملPalladium-catalyzed cyanation of aryl bromides promoted by low-level organotin compounds.
A novel method for palladium-catalyzed cyanation of aryl bromides promoted by low-level tri-n-butyltin chloride or cyanide is described. The method features low catalyst loading and mild reaction conditions. KCN is used as the cyanide source. Only trace levels of the tri-n-butyltin compound are required to achieve high conversion and yield in the cyanation of aryl bromides, iodides, and triflates.
متن کاملA new family of nucleophiles for photoinduced, copper-catalyzed cross-couplings via single-electron transfer: reactions of thiols with aryl halides under mild conditions (O °C).
Building on the known photophysical properties of well-defined copper-carbazolide complexes, we have recently described photoinduced, copper-catalyzed N-arylations and N-alkylations of carbazoles. Until now, there have been no examples of the use of other families of heteroatom nucleophiles in such photoinduced processes. Herein, we report a versatile photoinduced, copper-catalyzed method for c...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 13 39 شماره
صفحات -
تاریخ انتشار 2015